IE47232B1 - Soluble derivatives of 2,4-diamino-pyrimidines - Google Patents
Soluble derivatives of 2,4-diamino-pyrimidinesInfo
- Publication number
- IE47232B1 IE47232B1 IE1377/78A IE137778A IE47232B1 IE 47232 B1 IE47232 B1 IE 47232B1 IE 1377/78 A IE1377/78 A IE 1377/78A IE 137778 A IE137778 A IE 137778A IE 47232 B1 IE47232 B1 IE 47232B1
- Authority
- IE
- Ireland
- Prior art keywords
- pyrimidine
- diamino
- sodium
- compound
- general formula
- Prior art date
Links
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- -1 saturated aliphatic aldehydes Chemical class 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 239000011734 sodium Substances 0.000 claims description 11
- 159000000000 sodium salts Chemical class 0.000 claims description 11
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- LDBTVAXGKYIFHO-UHFFFAOYSA-N diaveridine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=CN=C(N)N=C1N LDBTVAXGKYIFHO-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 5
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 5
- XHPZVBGIPQQTQW-UHFFFAOYSA-N 5-benzylpyrimidine-2,4-diamine Chemical class NC1=NC(N)=NC=C1CC1=CC=CC=C1 XHPZVBGIPQQTQW-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 230000005587 bubbling Effects 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 239000011149 active material Substances 0.000 claims 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 4
- 239000004289 sodium hydrogen sulphite Substances 0.000 claims 3
- 235000010269 sulphur dioxide Nutrition 0.000 claims 2
- 239000004291 sulphur dioxide Substances 0.000 claims 2
- KEEYRKYKLYARHO-UHFFFAOYSA-N 5-[(4,5-dimethoxy-2-methylphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OC)=CC(C)=C1CC1=CN=C(N)N=C1N KEEYRKYKLYARHO-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 11
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 4
- 230000003389 potentiating effect Effects 0.000 abstract description 3
- 125000005055 alkyl alkoxy group Chemical group 0.000 abstract 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- 150000001299 aldehydes Chemical group 0.000 description 7
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229950000246 diaveridine Drugs 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- BWCYXTBCHPAVQY-GASJEMHNSA-N (3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxane-2-sulfonic acid Chemical compound S(=O)(=O)(O)C1(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO BWCYXTBCHPAVQY-GASJEMHNSA-N 0.000 description 2
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229940102223 injectable solution Drugs 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 2
- 125000001701 trimethoxybenzyl group Chemical group 0.000 description 2
- OOLOAWZLPBDRJQ-UHFFFAOYSA-N 2-benzylpyrimidine Chemical compound N=1C=CC=NC=1CC1=CC=CC=C1 OOLOAWZLPBDRJQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229940058936 antimalarials diaminopyrimidines Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- CCFMBGWTEFHSQA-UHFFFAOYSA-N ethanesulfonic acid pyrimidine Chemical compound CCS(O)(=O)=O.c1cncnc1 CCFMBGWTEFHSQA-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000008183 oral pharmaceutical preparation Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical compound CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 description 1
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical class NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- KQFAFFYKLIBKDE-UHFFFAOYSA-M sodium;ethanesulfonate Chemical compound [Na+].CCS([O-])(=O)=O KQFAFFYKLIBKDE-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- VLYWMPOKSSWJAL-UHFFFAOYSA-N sulfamethoxypyridazine Chemical compound N1=NC(OC)=CC=C1NS(=O)(=O)C1=CC=C(N)C=C1 VLYWMPOKSSWJAL-UHFFFAOYSA-N 0.000 description 1
- 229960004936 sulfamethoxypyridazine Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7722323A FR2397407A2 (fr) | 1977-07-11 | 1977-07-11 | Derives de 2,4-diamino pyrimidines et leur mise en solution en association avec des sulfamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE781377L IE781377L (en) | 1979-01-11 |
| IE47232B1 true IE47232B1 (en) | 1984-01-25 |
Family
ID=9193583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1377/78A IE47232B1 (en) | 1977-07-11 | 1978-07-10 | Soluble derivatives of 2,4-diamino-pyrimidines |
Country Status (13)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2502152A1 (fr) * | 1981-03-20 | 1982-09-24 | Panmedica Laboratoires | Nouveaux derives solubles n2 substitues de la diamino-2,4-benzyl-5-pyrimidines, leur procede de preparation et medicaments les contenant |
| US6583148B1 (en) | 1999-04-08 | 2003-06-24 | Krenitsky Pharmaceuticals, Inc. | Neurotrophic substituted pyrimidines |
| WO2002008205A1 (en) | 2000-07-24 | 2002-01-31 | Krenitsky Pharmaceuticals, Inc. | Substituted 5-alkynyl pyrimidines having neurotrophic activity |
| EP2343282B1 (en) | 2004-03-05 | 2015-07-22 | F. Hoffmann-La Roche AG | Diaminopyrimidines as P2X3 and P2X2/3 antagonists |
| CA2620129C (en) * | 2005-09-01 | 2014-12-23 | F. Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p2x2/3 modulators |
| WO2007025900A1 (en) * | 2005-09-01 | 2007-03-08 | F. Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p3x2/3 modulators |
| WO2007025899A1 (en) * | 2005-09-01 | 2007-03-08 | F. Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p2x2/3 modulators |
| KR101578949B1 (ko) * | 2007-10-08 | 2015-12-18 | 엠엠브이 메디슨즈 포 말라리아 벤처 | 가요성 측쇄를 가지는 항말라리아 화합물 |
| WO2012121682A2 (en) * | 2011-03-10 | 2012-09-13 | National Science And Technology Development Agency | Anti-folate antimalarials with dual-binding modes and their preparation |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2287071A (en) * | 1938-08-08 | 1942-06-23 | Parke Davis & Co | Organic amine derivatives and method of obtaining same |
| US2374791A (en) * | 1942-06-22 | 1945-05-01 | Parke Davis & Co | Organic amine derivatives and method of obtaining same |
| US3111521A (en) * | 1962-04-25 | 1963-11-19 | Parke Davis & Co | 2-aryl-nu-(polyamino-5-pyrimidinyl)-glycinonitriles |
| GB1375162A (enrdf_load_html_response) * | 1970-10-22 | 1974-11-27 | ||
| BE791627A (fr) * | 1971-11-20 | 1973-05-21 | Knapsack Ag | Procede pour l'oxydation du monoxyde de carbone et des hydrocarbures |
-
1977
- 1977-07-11 FR FR7722323A patent/FR2397407A2/fr active Granted
-
1978
- 1978-07-06 DE DE19782829820 patent/DE2829820A1/de not_active Withdrawn
- 1978-07-07 US US05/922,845 patent/US4232023A/en not_active Expired - Lifetime
- 1978-07-10 LU LU79949A patent/LU79949A1/xx unknown
- 1978-07-10 NL NL7807440A patent/NL7807440A/xx not_active Application Discontinuation
- 1978-07-10 IE IE1377/78A patent/IE47232B1/en unknown
- 1978-07-10 AT AT496978A patent/AT362381B/de active
- 1978-07-11 GB GB7829439A patent/GB2001965B/en not_active Expired
- 1978-07-11 BE BE2057136A patent/BE868893A/xx unknown
- 1978-07-11 ZA ZA00783957A patent/ZA783957B/xx unknown
- 1978-07-11 IT IT25569/78A patent/IT1096690B/it active
- 1978-07-11 JP JP8449678A patent/JPS5448776A/ja active Pending
- 1978-07-11 AU AU37933/78A patent/AU3793378A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU3793378A (en) | 1980-01-17 |
| FR2397407A2 (fr) | 1979-02-09 |
| LU79949A1 (fr) | 1979-04-09 |
| NL7807440A (nl) | 1979-01-15 |
| ATA496978A (de) | 1980-10-15 |
| ZA783957B (en) | 1979-09-26 |
| JPS5448776A (en) | 1979-04-17 |
| AT362381B (de) | 1981-05-11 |
| IE781377L (en) | 1979-01-11 |
| BE868893A (fr) | 1979-01-11 |
| FR2397407B2 (enrdf_load_html_response) | 1980-01-04 |
| US4232023A (en) | 1980-11-04 |
| DE2829820A1 (de) | 1979-02-01 |
| IT7825569A0 (it) | 1978-07-11 |
| GB2001965B (en) | 1982-03-10 |
| GB2001965A (en) | 1979-02-14 |
| IT1096690B (it) | 1985-08-26 |
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